Cuddy is touched by what he did, but is devastated when she spots him with a prostitute he employed, not understanding he had done so only to mess with Kutner and Taub. In the season finale “Both Sides Now” it’s confirmed that House wishes to pursue a romantic relationship with Cuddy. In this same episode he believes he has slept with Cuddy and informs Dr. James Wilson the following morning.
House has quietly admitted, at a number of situations, that he is grateful for Wilson’s presence, together with referring to Wilson as his best friend. When Wilson resigns and strikes away from both New Jersey and House’s friendship in the season 5 premiere, House is desperate to have his pal back, and hires a personal investigator (Michael Weston) to spy on him. The two finally reconcile at House’s father’s funeral in a scene much like their first …